When Keeping It Real Goes Wrong: How Discernment Should Be Your BFF in Job Seeking

As a producer of career-focused content, I’ve come across a diversity of information on best practices or advice for job seekers. Some insights are tried and true, while others are opinions that might not work for all —if at all. Oftentimes, job candidates—many who might be quite frustrated with what can be a grueling process—will take advisement one-dimensionally, not truly evaluating whether the information they’ve consumed applies to their unique situation or is even valid in the grand scheme of things.

A perfect example of this is when professionals take the “get creative” job-seeking strategy a bit too far, thinking it will guarantee they’ll stand out among thousands of candidates. They believe being radically out of the box will ensure cool points.

On the TODAY Show this morning, host Matt Lauer, along with attorney Star Jones, ad exec Donald “Donny” Deutsch, and money expert Suze Orman, discussed a bizarrely direct approach to cover letter writing. A candidate for a Wall Street internship wrote one detailing the following:

“I won’t waste your time inflating my credentials, throwing around exaggerated job titles, or feeding you a line of crapp [stet] about how my past experiences and skill set align perfectly for an investment banking internship. The truth is I have no unbelievably special skills or genius eccentricities, but I do have a near perfect GPA and will work hard for you.”

When asked whether they’d hire the person, Orman and Jones said no, with Jones referencing the misspelling of “crap” as a turn off and Orman saying the “no unbelievably special skills” quip as a red flag. Deutsch found the frankness “refreshing.”

That’s two out of three high-powered professionals giving that candidate’s chance at employment the can.

I’ve helped managers vet candidates and chosen some for job opportunities. While quite interesting—and almost clever—I wouldn’t have hired that person either. My line of thinking is consistent with Jones and Orman. (And I’ll add that if the candidate could put thought into writing such a cover letter, they could’ve put the same energy into showing, via creatively communicated and quantitative info, why their near-perfect GPA could translate into profit-making measures for that bank.)

The tone and nature of that letter gives employers a sense of that candidate’s personality, which in my opinion reads quite rude, nonchalant and elitist. It raises red flags in terms of how they’d do business with clients or customers, or how they’d relate with co-workers and managers.

I’m sure the person meant well, but this was a case of when keeping it too real goes wrong. Discernment must become one’s best friend when seeking opportunities.

Every piece of career development and job-seeking advice —like any advice—must be evaluated against a set of checkpoints. Does it align with the trends in your industry? Have you gotten the fundamentals down pat before trying to remix them? Have you had more than one person in your field analyze your job-seeking strategy and how you’re marketing yourself?

At the end of the day, it’s your life, so the final decision is yours. Be smart in how you take advisement, apply advice and make decisions you believe will take you to the top.